Manufacture of vat coloring matters



Patented June 19,1923.

' Umro STAT PATENT OFFICE.

- rmr menu, ormnnnm, cam; assrenon 'ro BADISCHE ANILIN- & sonarannrx, or IronwmsnmrEaton-mama, GERMANY, A CORPORATION or ena- Ho Drawing.

) To all whom it may concern:

Be it known that I, FILIP KAGER, citizen of the German Empire, residing at Mannheim, Germany, have invented new and use- 6 ful Improvements in the Manufacture of Vat Coloring Matters, of which the following is a specification.

I have found that very valuable vat coloring matters which are thiazol derivatives 1 of 2-amino-anthraquinone, can be obtained by condensing 1-mercapto-2-amino-anthraquinone or derivatives of this compound with an aromatic compound containing as substituents in its molecule at least two reactive carbon atoms, by which term I comprlse a carboxylic or aldehyde group, or their equivalents, carbonyl chlorid-COCI, dior trihalogen lmethyl groups and the like. The proportions should be such as to allow one molecular proportion of the last-named compound to react with two, or more, molecular proportions of the mercapto-aminoanthraquinone. Instead of the latter, 2- amino-anthraquinone and sulfur can sometimes be used.

Thedyestufis obtained according to this invention are characterized by giving violet hydrosulfite vats and dissolved in concentrated sulfuric acid with yellowish colors. By melting with caustic alkali the known fast blue vat dyestuif n-dihydro-anthraquinone-azine is produced and an aromatic polycarbonic acid.

By combining, for instance, one molecular proportion of terephaloyl-chlorid with two molecular proportions of l-mercapto-Q-amino-anthraquinone, a thiazol dyestufi is prolduced, represented by the following formu 8):

o o o o.

The following examples illustrate some uct 1s MANTIFACTURE OF VAT COLORING MATTERS.

Application filed January 4, 1923. Serial-No. 610,706.

modes of carrying the invention into elfect, but the invention is not limited to the examples. The parts are by weight Example 1.

Dissolve 10 parts of 1-mercapt0-2-aminoanthraquinone and 4 parts of terephthaloylchlorid in 100 parts of nitrobenzene and heat to boiling point. The solution which is first yellowish red, soon becomes yellow and the thiazol derivative separates out in the form of crystals, while hydrochloric acid gas is evolved. When the formation of thiazol no longer increases, the mass is moderately cooled, filtered and the residue washed with nitrobenzene and then with alcohol and dried. It is 'a yellow powder which is soluble in sulfuric acid with a reddish yellow color or with a yellow color when the prodfurther purified, for instance, by precipitating from sulfuric acid with a little water. With alkaline hydrosulfite solution a violet vat is produced, dyeing cotton lemon yellowshades. When subjected to a fusion with alkali, n-dihydro-anthraquinone-azine (indanthrene blue) andv terephthalic acid are produced. The same dye'stufi' is produced by heating m-tetraor m-hexa-chlon para-xylene with 2-amin0-anthraquinone and with sulfur.

When isophthaloyl-chloride is employed a yelloyiv dyestulf with a greenish tinge is obtaine E wam-ple 2.

E wample 3.

Boil together 10 parts of 1-mercapto-2- ami'no-anthraquinone, 6 parts of benzophenone-4.P-dicarboxylic acid chlorid and 100 parts of nitrobenzene until the formation of dyestmf is finished. Work up as described in example 1. The crude dye'stufi dissolves in concentrated sulfuric acid greenish yellow, in an alkaline hydrosulfite solution violet and dyes cotton yellow.

A similar product is obtained by employin benzophenone 2.4 dicarboxylic acid c'h orid in-lieu of the 4.4 -dica-rboxylic acid derivative.

Example 4.

Heat to from 140 degrees to 160 degrees centigradc, 25 parts of mesitylene and 150 parts of trichlorbenzcne and allow 300 parts of bromine to run in in the course of a few hours. Then expel the excess of bromine and introduce 150 parts of 1-mercapto;2- amino-anthraquinone and heat to boiling for 20 to 30 minutes. Work up as described in example 1. The dyestufi thus obtained gives a violet hydrosulfite vat from which cotton is dyed lemon yellow. Trimesinic acid chlorid can also be employed, the same product being obtained.

The dyestufi produced according to the above examples may be urified by heating with an alkaline hypoch orite solution.

I claim:

l. The process of manufacturing vat coloring matters characterized by condensing a l-mercapto-Qramino-anthraquinone body with an aromatic compound containing at least two reactive carbon atoms as substituents.

2. The process of manufacturing vat coloring matters, characterized by condensing about two molecular proportions of l-mer capto-2-amino-anthra uinone with one molecular pro ortion 0 an aromatic dicarboxylic aci chlorid.

3. The process of manufacturing a vat coloring matter which consists in acting on about two molecular proportions of l-mercapto-2-amino-anthraquinone with one 2110- v nasatae lecular proportion of a para xylene derivative of the formula.

in which R, means an oxy en atom, or two halogen atoms, and R hydrogen or a halogen atom, or a hydroxyl group.

4. As new articles of manufacture vat coloring matters which are thiazols derived from 1 mercapto 2-aminoanthraquinone and contain at least two such thiazol groups in their molecule and the residue of an aromatic acid containing at least two carboxylic groups, which coloring matters when treated in the alkali melt give n-dihydro anthraquinone-azinc (indanthrene blue) and w an aromatic polycarbonic acid, and which dyestufis dissolve in concentrated sulfuric acid with yellowish colors and dye cotton from a violet hydrosulfite vat yellow tints.

As a new article of manufacture a vat coloring matter corresponding to the formula Ctiifi which product when treated in the alkali 7 melt gives n-dihydro-anthra uinone-azine (indanthrene blue) and terep thalic acid, and which product dissolves in a pure state in concentrated sulfuric acid yellow and dyes cotton from a violet vat In testimony whereof lI-have hereunto set my hand.

FlLlP KACER.

yellow tints. to 

